Preparation of O,O-diethyl-O-(1-phenyl-2-cyano-prop-1-enyl)-thio

Details Preparation of O,O-diethyl-O-(1-phenyl-2-cyano-prop-1-enyl)-thio Preparation of O,O-diethyl-O-(1-phenyl-2-cyano-prop-1-enyl)-thio

1979-04-13

1980-08-26

Sutto, Anton H.

Chemistry of carbon compounds

Dipeptides, e.g., aspartame, anserine, carnosine, etc.

260940, C07F 9165

Patent

active

042195110

ABSTRACT:
In the preparation of O,O-diethyl-O-(1-phenyl-2-cyano-prop-1-enyl)-thionophosphoric acid ester by reacting a benzoic acid ester with propionitrile in the presence of an alkali metal alcoholate and then reacting the reaction mixture with O,O-diethyl-thionophosphoric acid diester chloride, the improvement which comprises employing about 5 to 50 moles of the propionitrile per mole of benzoic acid ester, distilling off the alcohol obtained during the reaction of propionitrile, benzoic acid ester and alcoholate before the addition of the O,O-diethyl-thionophosphoric acid diester chloride, and maintaining the volume of the reaction mixture approximately constant by adding propionitrile during the distillation. Advantageously the alcoholate is sodium methylate, ethylate or tert.-butylate or potassium methylate, ethylate or tert.-butylate, the reaction is effected at about 80.degree. to 120.degree. C., about 5 to 25 moles of propionitrile are employed per mole of benzoic acid ester, about 1 to 1.3 moles of benzoic acid ester and about 1 to 1.15 moles of alkali metal alcoholate are employed per mole of O,O-diethyl-thionophosphoric acid diester chloride, and the benzoic acid ester is the methyl ester or ethyl ester.

REFERENCES:
patent: 3775517 (1973-11-01), Riebel et al.
Conant et al., "The Chemistry of Organic Compounds", Third Edition, Macmillan Co., N.Y., (1947), pp. 93-94.

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